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thionyl dichloride 7719-09-7
Cas No: 7719-09-7
No Data No Data No Data Hunan Russell Chemicals Technology Co.,Ltd Contact Supplier
Thionyl chloride
Cas No: 7719-09-7
No Data No Data No Data ZHENFEI INDUSTRY CO.,LTD Contact Supplier
Thionyl chloride
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Thionyl chloride Manufacturer in stock
Cas No: 7719-09-7
No Data 300 Kilogram 20 Metric Ton/Month Jiangxi Sunway Chemical Co. Ltd. Contact Supplier

7719-09-7 Usage

Health Hazard

CORROSIVE and/or TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Fire will produce irritating, corrosive and/or toxic gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control or dilution water may cause pollution.

Toxicity

Thionyl chloride is toxic and is corrosive and has tearing property.
Pathways: inhaled, ingested, percutaneous absorption.
Health hazard: inhalation, oral administration or percutaneous absorption is harmful to our health. The eyes, skin, mucosa and respiratory tract have a strong stimulating effect and can cause burn wound. After inhalation, it may be lethal due to causing the spasm and dropsy of throat and bronchial. Poisoning performance includes burning sensation, coughing, wheezing, and dizziness, and laryngitis, shortness of breath, headache, nausea and vomiting.
Acute toxicity: LC50: 2435 mg/m3 (rat inhalation)
Irritation: a rabbit eyes: 1380 μg, severe stimulation.
Protective: This product can burn the skin and is irritable to the mucous membrane. During operation, the worker should wear protective equipment and should wash immediately with plenty of water if being splashed on skin.
First-aid
Skin contact: Immediately remove contaminated clothing, rinse with plenty of water for at least 15 minutes. Then go for medical treatment.
Eye contact: immediately lift up eyelid; wash with large flows of water or saline thoroughly for at least 15 minutes. Then go for medical treatment.
Inhalation: rapidly leave the scene to place with fresh air. Keep the airway open. If breathing is difficult, give oxygen. If breathing stops, immediately apply artificial respiration and send for medical treatment.
Ingestion: for misusage people, immediately rinse the mouth with water and drink milk or egg white. Then go for medical treatment.

Toxicity grading

highly toxic

Reactivity Profile

Thionyl chloride reacts, potentially explosively, with dimethyl sulfoxide or dimethylformamide containing traces of iron or zinc [Spitulnik, M. J., Chem. Eng. News, 1977, 55(31), p. 31]. Undergoes violent reactions with bases (ammonia, sodium hydroxide, potassium hydroxide, amines), alkali metals (sodium, potassium), esters (ethyl acetate), toluene mixed with ethanol / water [Bretherick, 5th ed., 1995, p. 1325]. Has an expansion ratio from gas to liquid of nearly 1000:1. Hence may cause an explosion if heated while contained [MCA Case History No. 1808]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Perchloric acid ignites on contact with sulfinyl chloride. (Bailar, 1973, Vol. 2, 1442). SOCl2 reacts with esters, such as ethyl acetate, forming toxic SO2 gas and water soluble/toxic acyl chlorides, catalyzed by Fe or Zn (Spagnuolo, C.J. et al. 1992. Chemical and Engineering News 70(22):2.).

Purification

Thionyl chloride crude product often contains impurities including sulfuryl chloride, sulfur monochloride and sulfur dichloride. In order to obtain a higher purity of thionyl chloride, sulfur powder has to be added for refluxing and distillation to obtain high-purity chloride sulfoxide. The detailed mechanisms of reactions remain to be unclear. According to my analysis, it may be that it can prevent the thionyl chloride being decomposed into sulfur dichloride, sulfur dioxide and chlorine during the process of distillation. The detailed purification method is that: put together of 450 ml of thionyl chloride with 12.5g of sulfur powder for being heated under reflux for 4.5 hours, followed by efficient fractionating column for twice to obtain pure colorless. Alternatively, you can also apply distillation purification in the presence of triphenyl phosphite. The removed impurities should be sulfuryl chloride, sulfur monochloride and sulfur dichloride.

Chemical Properties

Colorless to slightly yellow liquid

Production method

It can be produced with the reaction between sulfur trioxide and sulfur dichloride.
Chlorosulfonic acid method: first add sulfur powder to the reactor, put through the chlorine gas for reaction to generate sulfur monochloride. Then add a certain amount of chlorine acid and sulfur monochloride to the reactor; put through chlorine gas at below 50 ℃ for reaction; the resulted mixture was further subject to the crude distillation and condensation; further collect the material liquid below 130 ℃ and feed to the distillation pot; in order to make the low-boiling sulfur dichloride be convert to sulfur chloride for further being left in the pot, then you have to add 15% to 20% the amount of the crude product of sulfur and then send for distillation; reflux for 4h until giving normal color; collect the fraction between 75-80 ℃ to obtain the finished product. The reaction equation is:
2ClSO3H + S2C12 + C12 → 2SOC12 + 2SO2 + 2HCl
Sulfur dioxide method: take sulfur, liquid chlorine and liquid sulfur dioxide as raw material; apply whole-cycle and liquid circulation method for production of high-purity alumina thionyl chloride with a purity of 99%; this method has advanced technology, high product quality and releases less "three wastes".

Chemical Properties

It is colorless or light yellow volatile liquid with a strong suffocating odor. It can also be miscible with benzene, chloroform and carbon tetrachloride.

Uses

Thionyl chloride is an important intermediate of organic chemistry and is mainly used in medicine, pesticides, dyes and industrial organic synthesis industry as chlorinating agent. Consumption structure: the pharmaceutical industry accounted for 25%, pesticide industry accounted for 50%, dyestuff industry accounted for 5% and other industries accounted for 20%. The pesticide industry contributes the major part for consumption of thionyl chloride and is mainly used for the production of inabenfide, valerate, fenvalerate, mosquito-killing dimerthrin, flucythrinate, diflubenzuron, isocarbophos, fenpropathrin, endosulfan, deltamethrin, a (b) group chlorpyrifos, oxazolidinone, quizalofop and warfarin.
Because thionyl chloride can have fierce reaction with water, it is able to have reaction with metal chloride hydrated salt for production with anhydrous metal chlorides. MCln ? xH2O + x SOCl2 → MCln + x SO2 + 2x HCl
Thionyl chloride was subjected heating reflux with a transition metal oxide and can further generate the corresponding oxychloride of the metal: WO3 + 2SOCl2 → WOCl4 + 2SO2
Thionyl chloride has been widely used for converting alcohol and the carboxylic acid into the corresponding acid chloride and chlorinated hydrocarbons. Compared with other agents (such as phosphorus penta-chloride), thionyl chloride is often the preferred reagents, because both the reaction product of sulfur dioxide and hydrogen chloride are gaseous and is easily to be separated. The excess amount of thionyl chloride can be removed by distillation. RC (= O)-OH + O = SCl2 → RC (= O)-Cl + SO2 + HCl R-OH + O = SCl2 → R-Cl + SO2 + HCl. Sulfoacid can react with thionyl chloride to generate sulfonyl chloride. Sulfinic acid can have reaction with thionyl chloride to generate sulfinyl chloride. Phosphonic acid can have reaction with thionyl chloride to generate phosphine chloride.
Thionyl chloride can react with mono-substituted formamide to generate the corresponding isonitriles. Amide can react with thionyl chloride to generate imine acyl chloride. Primary amide, upon co-heating with thionyl chloride, will be further dehydrated to become nitrile.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Storage characteristics

Treasury ventilation low-temperature drying; and bases, food additives stored separately;

Packing and storage

Packaging: glass or plastic barrels (tank) full open drums; glass or plastic bucket (cans); outside: the ordinary wooden box or wooden grille half; frosted glass bottles or threaded glass; outside: the ordinary wooden box; ampoules; outside: ordinary wooden box.
Storage precautions: for railway transport, it should be subject to package strictly in accordance with the dangerous cargo form in the <> (Ministry of railway of china). Upon the shipment, the packaging should be complete and the loading should be safe. During the process of transport, we should ensure that the container does not leak, does not fall off and does not been broken. It is not allowed to mix it with alkali or edible chemicals for operation and transport. During the transport, the transport vehicles should be equipped with spill response equipment. During the transport process, we should prevent sunshine exposure, rain and high temperature. During the road transport, the vehicles should be driven according to the provided routes with no stopping in residential areas and densely populated areas. It should be stored in a cool, ventilated warehouse with the storage temperature being not exceed 25 ℃ and the relative humidity being less than 75%. Keep the container closed. Moreover, we should store it separately from bases and avoid mixing for storage. Storage areas should be equipped with spill response equipment and suitable host materials.

Purification Methods

Crude SOCl2 can be freed from sulfuryl chloride, sulfur monochloride and sulfur dichloride by refluxing it with sulfur and then fractionally distilling twice. [The SOCl2 is converted to SO2 and sulfur chlorides. The S2Cl2 (b 135.6o) is left in the residue, whereas SCl2 (b 59o) passes over in the forerun.] The usual purification is to distil it from quinoline (50g SOCl2 to 10g quinoline) to remove acid impurities, followed by distillation from boiled linseed oil (50g SOCl2 to 20g of oil). Precautions must be taken to exclude moisture. Thionyl chloride is used extensively in organic syntheses and can be prepared by distillation of technical SOCl2 in the presence of diterpene (12g/250mL SOCl2), and avoiding overheating. Further purification is achieved by redistillation from linseed oil (1-2%) [Rigby Chem Ind (London) 1508 1969]. Gas chromatographically pure material is obtained by distillation from 10% (w/w) triphenyl phosphite [Friedman & Wetter J Chem Soc (A) 36 1967, Larsen et al. J Am Chem Soc 108 6950 1986]. HARMFUL VAPOURS.

Synthesis method

Currently there are major approaches for industrial production of thionyl chloride including chlorosulfonic acid method, sulfur dioxide gas-phase method and phosphorus oxychloride cogeneration.
Fixed consumption amount:
Production methods raw material and specifications consumption quota/t ? t-1
Chlorosulfonic acid method chlorosulfonic acid (95%) 1.1
Liquid chlorine (99%) 0.91
Sulfur powder (99.5%) 0.42
Fumed sulfur dioxide (99.5%) 0.22
Liquid chlorine (99%) 0.88
Sulfur dioxide (99%) 0.44
Cogeneration phosphorus oxychloride, phosphorus trichloride (98%) 1.3
Liquid chlorine (99%) 0.66
Sulfur dioxide (99%) 0.64

Acute toxicity

inhalation-rat LC50: 500 PPM/1 hour

Uses

For making acyl chlorides, to replace OH or SH groups with chlorine atoms; reacts with Grignard reagents to form the corresponding sulfoxides. Review of use in organic synthesis: J. S. Pizey, Synthetic Reagents vol. 1 (John Wiley, New York, 1974) pp 321-357.

Category

corrosive materials

Hazard

Strong irritant to skin, tissue, and upper respiratory tract.

How to deal with the wasted thionyl chloride so that the environ

It is recommended for distillation recycling. If you want to deal with it, you can add it slowly into ice water for decomposition into SO2 and HCL which are subject to further treatment.
If the amount of the wasted thionyl chloride is large, you can consider recycle or sold outside for treatment. If the amount is small, you can add it drop wise into the alkaline water for decomposition and neutralization.

Fire Hazard

EXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily. May ignite combustibles (wood, paper, oil, clothing, etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases and runoff. Flammable/toxic gases may accumulate in confined areas (basement, tanks, hopper/tank cars, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. Substance may be transported in a molten form.

Professional standards

TWA 1 PPM (5 mg/cubic meter); STEL 1 PPM (5 mg/m3)

Outline

Thionyl chloride, at room temperature and pressure, is a colorless or pale yellow liquid with a pungent odor. It has a relative density of 1.676, melting point of-104.5 ℃ and the boiling point of 78.8 ℃. Upon coming across water, it is easily decomposed into sulfur dioxide and hydrogen chloride. It is soluble in benzene, chloroform and carbon tetrachloride. It begins to decompose upon being heated to 150 °C with complete decomposition at 500°C. Thionyl chloride sometimes can be easily confused with thionyl chlorine (SO2Cl2). However, these two compounds actually have a large difference in their chemical nature with its chlorine atom having a strong substitution capacity on hydroxyl group or sulfur group. Thionyl chloride can form corresponding chlorides with hydroxyl-containing phenol or hydroxyl-containing alcohol to form the corresponding chlorides; it can have reaction with Grignard reagent to generate the corresponding sulfoxide compound. The molecular structure of thionyl chloride is cone type wherein the sulfur (VI) center contains one lone pair of electrons. However, COCl2 has planar configuration. Owing to the strong reaction between the thionyl chloride and water, SOCl2 does not exist in nature.

Uses

It can be applied to medicine, pesticide and dye industries and mainly used for the production of isocarbophos, sumicidin, propargite tetramisole hydrochloride, indomethacin, and vitamin A, etc.
It can be used as the chlorinating agents for organic synthesis such as chlorination of alcoholic hydroxyl group, chlorination of carboxylic acid, chlorination of acid anhydride and the chlorine displacement of organic sulfonic acid or carboxylic acid. It can also be used for making acyl chloride as well as being used for the manufacture of pharmaceutical intermediates such as tetramisole hydrochloride and synthomycin palmitate. It can also be used as a dehydrating agent or solvent.

Extinguishing agent

dry sand, dry powder; water ban

Flammability and hazard characteristics

irritation; meeting with water can emit toxic sulfur dioxide, hydrogen chloride, chlorine and other gases; thermal decomposition can generate toxic fumes of sulfur oxides and chlorides

General Description

A colorless to yellow fuming liquid with a suffocating pungent odor. Boiling point 79°C. A lachrymator. Highly corrosive and toxic. Long-term inhalation of low concentrations or short-term inhalation of high concentrations has adverse health effects.
InChI:InChI=1/Cl2OS/c1-4(2)3

7719-09-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (41868)  Thionyl chloride, 99+%    7719-09-7 *2x1kg 1456.0CNY Detail
Alfa Aesar (41868)  Thionyl chloride, 99+%    7719-09-7 500g 647.0CNY Detail
Alfa Aesar (41868)  Thionyl chloride, 99+%    7719-09-7 50g 105.0CNY Detail
Alfa Aesar (H31857)  Thionyl chloride, 1M soln. in dichloromethane    7719-09-7 500ml 775.0CNY Detail
Alfa Aesar (H31857)  Thionyl chloride, 1M soln. in dichloromethane    7719-09-7 100ml 433.0CNY Detail

7719-09-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name thionyl dichloride

1.2 Other means of identification

Product number -
Other names Thionyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7719-09-7 SDS

7719-09-7Synthetic route

sulfur dichloride
10545-99-0

sulfur dichloride

sulfur trioxide
7446-11-9

sulfur trioxide

A

thionyl chloride
7719-09-7

thionyl chloride

B

sulfur dioxide
7446-09-5

sulfur dioxide

Conditions
ConditionsYield
In neat (no solvent) below -10°C or under pressure;;A 100%
B n/a
hydrogenchloride
7647-01-0

hydrogenchloride

N-phenylsulfinylamine
222851-56-1

N-phenylsulfinylamine

A

thionyl chloride
7719-09-7

thionyl chloride

B

aniline hydrochloride
142-04-1

aniline hydrochloride

Conditions
ConditionsYield
In Petroleum ether decompn. of thioaniline dissolved in dild. petroleum (b.p. 200-250°C) on introduction of dry HCl (shaking) at -10°C;; filtration (anilinium chloride); fractionation;;A 94%
B n/a
sulfur dichloride
10545-99-0

sulfur dichloride

sulfur trioxide
7446-11-9

sulfur trioxide

A

thionyl chloride
7719-09-7

thionyl chloride

B

pyrosulfuryl chloride
7791-27-7

pyrosulfuryl chloride

C

sulfur dioxide
7446-09-5

sulfur dioxide

Conditions
ConditionsYield
In neat (no solvent) SO3 is distilled (from 65 % oleum) into cooled (ice/water) vessel containing SCl2; evolution of SO2;; multiple fractionation (at last in presence of sulfur);;A 80%
B n/a
C n/a
tetrachloromethane
56-23-5

tetrachloromethane

A

phosgene
75-44-5

phosgene

B

thionyl chloride
7719-09-7

thionyl chloride

Conditions
ConditionsYield
With sulfur dioxide In neat (no solvent) reaction of CCl4 with SO2 on heating to 200°C;;A n/a
B 72%
Ethanesulfonyl chloride
594-44-5

Ethanesulfonyl chloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

chloroethane
75-00-3

chloroethane

C

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
at 200 - 210℃;
tetrachloromethane
56-23-5

tetrachloromethane

aluminium trichloride
7446-70-0

aluminium trichloride

SO2

SO2

thionyl chloride
7719-09-7

thionyl chloride

Conditions
ConditionsYield
at 200℃; unter Druck;
carbon disulfide
75-15-0

carbon disulfide

hypochlorous acid anhydride

hypochlorous acid anhydride

A

phosgene
75-44-5

phosgene

B

thionyl chloride
7719-09-7

thionyl chloride

phosgene
75-44-5

phosgene

SO2

SO2

A

thionyl chloride
7719-09-7

thionyl chloride

B

carbon dioxide
124-38-9

carbon dioxide

C

sulfur chloride

sulfur chloride

Conditions
ConditionsYield
at 200 - 400℃;
Trichloromethanesulfonyl chloride
2547-61-7

Trichloromethanesulfonyl chloride

A

tetrachloromethane
56-23-5

tetrachloromethane

B

phosgene
75-44-5

phosgene

C

thionyl chloride
7719-09-7

thionyl chloride

D

sulfur dioxide

sulfur dioxide

Conditions
ConditionsYield
at 200℃;
aluminium trichloride
7446-70-0

aluminium trichloride

chloroform
67-66-3

chloroform

SO2

SO2

thionyl chloride
7719-09-7

thionyl chloride

Conditions
ConditionsYield
at 150℃;
diethyl sulphite
623-81-4

diethyl sulphite

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

ethyl chlorosulfite
6378-11-6

ethyl chlorosulfite

C

chloroethane
75-00-3

chloroethane

Conditions
ConditionsYield
bei niedrigerer Temperatur;
dipropyl sulfite
623-98-3

dipropyl sulfite

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

1-Chloropropane
540-54-5

1-Chloropropane

Conditions
ConditionsYield
beim Erwaermen;
sulfurous acid dibutyl ester
626-85-7

sulfurous acid dibutyl ester

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

n-Butyl chloride
109-69-3

n-Butyl chloride

Conditions
ConditionsYield
bei schwachem Erwaermen;
aluminium trichloride
7446-70-0

aluminium trichloride

sulfuryl dichloride
7791-25-5

sulfuryl dichloride

1,2,4,5-tetrachlorobenzene
95-94-3

1,2,4,5-tetrachlorobenzene

disulfur dichloride

disulfur dichloride

A

tetrachloromethane
56-23-5

tetrachloromethane

B

thionyl chloride
7719-09-7

thionyl chloride

C

pentachlorobenzene
608-93-5

pentachlorobenzene

D

hexachlorobenzene
118-74-1

hexachlorobenzene

ethyl chlorosulfite
6378-11-6

ethyl chlorosulfite

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

chloroethane
75-00-3

chloroethane

Conditions
ConditionsYield
at 25℃;
p-hydoroxybenzenesulfonic acid
98-67-9

p-hydoroxybenzenesulfonic acid

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

para-dichlorobenzene
106-46-7

para-dichlorobenzene

C

4-chlorophenylphosphorodichloridate
772-79-2

4-chlorophenylphosphorodichloridate

Conditions
ConditionsYield
Reaktion des Kaliumsalzes;
diethyl sulphite
623-81-4

diethyl sulphite

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

chloroethane
75-00-3

chloroethane

C

SO2

SO2

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

4,4'-sulfonyl-bis-benzenesulfonyl chloride
32337-45-4

4,4'-sulfonyl-bis-benzenesulfonyl chloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

para-dichlorobenzene
106-46-7

para-dichlorobenzene

D

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

1-Naphthalenesulfonyl chloride
85-46-1

1-Naphthalenesulfonyl chloride

A

thionyl chloride
7719-09-7

thionyl chloride

C

1-Chloronaphthalene
90-13-1

1-Chloronaphthalene

Conditions
ConditionsYield
at 150 - 160℃;
phenyltetrachlorophosphorane
4895-65-2

phenyltetrachlorophosphorane

sulfur dioxide

sulfur dioxide

A

P,P-dichlorophenylphosphine oxide
824-72-6

P,P-dichlorophenylphosphine oxide

B

thionyl chloride
7719-09-7

thionyl chloride

phenyl chlorosulphinate
13165-73-6

phenyl chlorosulphinate

A

thionyl chloride
7719-09-7

thionyl chloride

B

diphenyl sulfite
4773-12-0

diphenyl sulfite

Conditions
ConditionsYield
at 70℃; Einleiten von HCl;
phenyl chlorosulphinate
13165-73-6

phenyl chlorosulphinate

A

thionyl chloride
7719-09-7

thionyl chloride

B

phosphoric acid triphenyl ester
115-86-6

phosphoric acid triphenyl ester

2-benzoylamino-[1]naphthoic acid
861087-97-0

2-benzoylamino-[1]naphthoic acid

A

thionyl chloride
7719-09-7

thionyl chloride

B

2-benzoyl-2H-naphth[2,1-b]azet-1-one

2-benzoyl-2H-naphth[2,1-b]azet-1-one

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

2,2'-sulfonyl-bis-benzenesulfonyl chloride

2,2'-sulfonyl-bis-benzenesulfonyl chloride

A

thionyl chloride
7719-09-7

thionyl chloride

B

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

Conditions
ConditionsYield
at 200 - 210℃;
tetrachloro-dipropylamino-phosphorane; compound with phosphorus pentachloride

tetrachloro-dipropylamino-phosphorane; compound with phosphorus pentachloride

SO2

SO2

A

thionyl chloride
7719-09-7

thionyl chloride

B

N,N-dipropylphosphoramidic dichloride
40881-98-9

N,N-dipropylphosphoramidic dichloride

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

phenyl-methanesulfonic acid ; potassium salt

phenyl-methanesulfonic acid ; potassium salt

A

thionyl chloride
7719-09-7

thionyl chloride

B

benzyl chloride
100-44-7

benzyl chloride

2',2',2'-Trichloroethyl 3-methyl-2-[2-chlorosulfinyl-4-oxo-3-(2-tert-butoxycarbonylamino-2-phenylacetamido)-1-azetidinyl]-3-butenoate

2',2',2'-Trichloroethyl 3-methyl-2-[2-chlorosulfinyl-4-oxo-3-(2-tert-butoxycarbonylamino-2-phenylacetamido)-1-azetidinyl]-3-butenoate

A

thionyl chloride
7719-09-7

thionyl chloride

B

2',2',2'-Trichloroethyl 3-methyl-2-[2-sulfino-4-oxo-3-(2-tert-butoxycarbonylamino-2-phenylacetamido)-1-azetidinyl]-3-butenoate

2',2',2'-Trichloroethyl 3-methyl-2-[2-sulfino-4-oxo-3-(2-tert-butoxycarbonylamino-2-phenylacetamido)-1-azetidinyl]-3-butenoate

Conditions
ConditionsYield
In acetone
carbon disulfide
75-15-0

carbon disulfide

hypochlorous anhydride
7791-21-1

hypochlorous anhydride

A

phosgene
75-44-5

phosgene

B

thionyl chloride
7719-09-7

thionyl chloride

Conditions
ConditionsYield
In tetrachloromethane CS2 dild. in CCl4 (to diminuish vehemence of reaction);;
In tetrachloromethane
thionyl chloride
7719-09-7

thionyl chloride

(S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochloric acid salt

(S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochloric acid salt

methyl (S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylate hydrochloric acid salt
114786-39-9

methyl (S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylate hydrochloric acid salt

Conditions
ConditionsYield
In methanol for 3.5h; Heating / reflux;100%
thionyl chloride
7719-09-7

thionyl chloride

bis(tetrabutylammonium) hexatungstate

bis(tetrabutylammonium) hexatungstate

N(C4H9)4(1+)*WOCl5(1-) = [N(C4H9)4][WOCl5]

N(C4H9)4(1+)*WOCl5(1-) = [N(C4H9)4][WOCl5]

Conditions
ConditionsYield
In thionyl chloride (argon); stirring (ca. 16 h); pptn. with Et2O, washing (Et2O), drying (vac.);100%
thionyl chloride
7719-09-7

thionyl chloride

tetrabutylammonium decatungstate ammonium salt

tetrabutylammonium decatungstate ammonium salt

N(C4H9)4(1+)*WOCl5(1-) = [N(C4H9)4][WOCl5]

N(C4H9)4(1+)*WOCl5(1-) = [N(C4H9)4][WOCl5]

Conditions
ConditionsYield
In thionyl chloride (argon); stirring (ca. 16 h); pptn. with Et2O, washing (Et2O), drying (vac.);100%
thionyl chloride
7719-09-7

thionyl chloride

(5,7,12,14-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinate(2-))V=O

(5,7,12,14-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinate(2-))V=O

(5,7,12,14-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinate(2-))VCl2
173105-66-3

(5,7,12,14-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinate(2-))VCl2

Conditions
ConditionsYield
In dichloromethane (Ar); react. (0°C), warming (room temp.), stirring (6 h), solventevapn.; washing (diethyl ether, pentane), drying (high vacuum, 50°C, 8 h);100%
thionyl chloride
7719-09-7

thionyl chloride

Se4(1+)*[MoOCl4](1-)=Se4[MoOCl4]

Se4(1+)*[MoOCl4](1-)=Se4[MoOCl4]

[SeCl3][MoOCl4], β

[SeCl3][MoOCl4], β

Conditions
ConditionsYield
In thionyl chloride vac., 150°C, 3 d;100%
thionyl chloride
7719-09-7

thionyl chloride

2-(2,6-dichlorophenyl)acetic acid
6575-24-2

2-(2,6-dichlorophenyl)acetic acid

1-bromo-3-(2,6-dichlorophenyl)propan-2-one
880089-70-3

1-bromo-3-(2,6-dichlorophenyl)propan-2-one

Conditions
ConditionsYield
Stage #1: thionyl chloride; 2-(2,6-dichlorophenyl)acetic acid With diazomethyl-trimethyl-silane
Stage #2: With hydrogen bromide In water
100%
thionyl chloride
7719-09-7

thionyl chloride

C14H12Cl2N2O3S
1218941-06-0

C14H12Cl2N2O3S

C14H11Cl3N2O2S
1218941-07-1

C14H11Cl3N2O2S

Conditions
ConditionsYield
100%
thionyl chloride
7719-09-7

thionyl chloride

4-[1-(trifluoroacetyl)piperidin-4-yl]benzoic acid
1376437-09-0

4-[1-(trifluoroacetyl)piperidin-4-yl]benzoic acid

4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzoyl chloride
1331747-36-4

4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzoyl chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 70℃; for 5h; Sealed tube;100%
thionyl chloride
7719-09-7

thionyl chloride

dimer acid
47818-40-6

dimer acid

C36H62Cl2O2

C36H62Cl2O2

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 35℃; for 4h; Inert atmosphere;100%
thionyl chloride
7719-09-7

thionyl chloride

cobalt(II) 2,9,16,23-phthalocyanine tetrasulfonic acid

cobalt(II) 2,9,16,23-phthalocyanine tetrasulfonic acid

cobalt[2,9,16,23-tetrakis(chlorosulfonyl)]phthalocyanine

cobalt[2,9,16,23-tetrakis(chlorosulfonyl)]phthalocyanine

Conditions
ConditionsYield
at 80℃; for 12h;100%
methanol
67-56-1

methanol

thionyl chloride
7719-09-7

thionyl chloride

4-nitro-1H-pyrazole-3-carboxylic acid
5334-40-7

4-nitro-1H-pyrazole-3-carboxylic acid

methyl 4-nitro-1H-pyrazole-3-carboxylate
138786-86-4

methyl 4-nitro-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
at 0 - 25℃; for 16 - 48h; Product distribution / selectivity;99.5%
silver(I) nitrite
7783-99-5

silver(I) nitrite

thionyl chloride
7719-09-7

thionyl chloride

A

nitrosylchloride
2696-92-6

nitrosylchloride

B

silver(I) chloride

silver(I) chloride

Conditions
ConditionsYield
In diethyl ether byproducts: SO2; to finely ground dry Ag salt in anhyd. Et2O cooled to 0°C added dropwise with vigorous stirring equimolar amt. of thionyl chloride; suspn. stirred for 15 min; soln. was decanted from AgCl; AgCl dried; soln. washed (Et2O); all extracts combined; cooled to 0°C;A n/a
B 99%
thionyl chloride
7719-09-7

thionyl chloride

silver nitrate

silver nitrate

A

Nitryl chloride

Nitryl chloride

B

nitrosylchloride
2696-92-6

nitrosylchloride

C

silver(I) chloride

silver(I) chloride

Conditions
ConditionsYield
In diethyl ether byproducts: SO2, SO3; to finely ground dry Ag salt in anhyd. Et2O cooled to 0°C added dropwise with vigorous stirring equimolar amt. of thionyl chloride; suspn. stirred for 15 min; soln. was decanted from AgCl; AgCl dried; soln. washed (Et2O); all extracts combined; cooled to 0°C;A n/a
B n/a
C 99%
thionyl chloride
7719-09-7

thionyl chloride

(4,4'-dicarboxy-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride dihydrate

(4,4'-dicarboxy-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride dihydrate

(4,4'-bis(chlorocarbonyl)-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride*SOCl2*HCl

(4,4'-bis(chlorocarbonyl)-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride*SOCl2*HCl

Conditions
ConditionsYield
In dichloromethane (N2); stirring (4 h, reflux); solvent removal (reduced pressure), drying (vac., 60-70 degree.C, 1 h); elem. anal.;99%
thionyl chloride
7719-09-7

thionyl chloride

tributylammonium dodecaborododecahydride

tributylammonium dodecaborododecahydride

2(C4H9)3NH(1+)*B12H9(SO)3(2-)=((C4H9)3NH)2(B12H9(SO)3)

2(C4H9)3NH(1+)*B12H9(SO)3(2-)=((C4H9)3NH)2(B12H9(SO)3)

Conditions
ConditionsYield
In dichloromethane SOCl2 added to CH2Cl2 soln. of B compd. (molar ratio 1:3, 1:4); concd. slowly; ppt. purified by column chromy. (silica gel, CH2Cl2);99%
In neat (no solvent) excess of SOCl2 added to B compd.; purified by column chromy. (silica gel, CH2Cl2);99%
In dichloromethane SOCl2 added to CH2Cl2 soln. of B compd. (molar ratio 2:1, 1:1, 1:2); concd. slowly; mixt. of the starting B compd. and title compd. pptd.; purified by column chromy. (silica gel, CH2Cl2);15%
thionyl chloride
7719-09-7

thionyl chloride

[(C5(CH3)5)TiCl(C5H4C(CH3)2CH2CO2)]
864767-27-1

[(C5(CH3)5)TiCl(C5H4C(CH3)2CH2CO2)]

[(C5(CH3)5)TiCl2(C5H4C(CH3)2CH2COCl)]
864767-39-5

[(C5(CH3)5)TiCl2(C5H4C(CH3)2CH2COCl)]

Conditions
ConditionsYield
In not given99%
thionyl chloride
7719-09-7

thionyl chloride

chloro(cyclopentadienyl)(cyclopentadienyl-3-methyl-3-butanoate)titanium(IV)
864766-99-4

chloro(cyclopentadienyl)(cyclopentadienyl-3-methyl-3-butanoate)titanium(IV)

Cp(CpCMe2CH2COCl)titanium(IV)dichloride
864767-00-0

Cp(CpCMe2CH2COCl)titanium(IV)dichloride

Conditions
ConditionsYield
In not given99%
In neat (no solvent) at 20℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;
thionyl chloride
7719-09-7

thionyl chloride

[(C5H5)TiCl(C5H4C(CH2)5CH2CO2)]
864767-24-8

[(C5H5)TiCl(C5H4C(CH2)5CH2CO2)]

[(C5H5)TiCl2(C5H4C(CH2)5CH2COCl)]
864767-36-2

[(C5H5)TiCl2(C5H4C(CH2)5CH2COCl)]

Conditions
ConditionsYield
In not given99%
thionyl chloride
7719-09-7

thionyl chloride

chloro(cyclopentadienyl)(cyclopentadienyl-3-methyl-3-butanoate)titanium(IV)
864766-99-4

chloro(cyclopentadienyl)(cyclopentadienyl-3-methyl-3-butanoate)titanium(IV)

cholesterol
57-88-5

cholesterol

[(C5H5)TiCl2(C5H4C(CH3)2CH2CO2C27H45)]

[(C5H5)TiCl2(C5H4C(CH3)2CH2CO2C27H45)]

Conditions
ConditionsYield
With sodium hydride In dichloromethane mixt. of Ti complex and SOCl2 was stirred for 3 h; evapd. (vac., 80°C); dissolved in CH2Cl2; added to mixt. of NaH and cholesterol; stirred for 16 h; filtered; solvent removed (vac.); crystd. (CH2Cl2);99%
thionyl chloride
7719-09-7

thionyl chloride

[(C5H5)TiCl(C5H4C(CH3)2CH2CH2CO2)]
1122084-99-4

[(C5H5)TiCl(C5H4C(CH3)2CH2CH2CO2)]

cholesterol
57-88-5

cholesterol

[(C5H5)TiCl2(C5H4C(CH3)2(CH2)2CO2C27H45)]

[(C5H5)TiCl2(C5H4C(CH3)2(CH2)2CO2C27H45)]

Conditions
ConditionsYield
With sodium hydride In dichloromethane mixt. of Ti complex and SOCl2 was stirred for 3 h; evapd. (vac., 80°C); dissolved in CH2Cl2; added to mixt. of NaH and cholesterol; stirred for 16 h; filtered; solvent removed (vac.); crystd. (CH2Cl2);99%
thionyl chloride
7719-09-7

thionyl chloride

(4R,5S)-5-phenylthio-4-octanol
1202357-35-4

(4R,5S)-5-phenylthio-4-octanol

((4S,5R)-5-chlorooctan-4-yl)(phenyl)sulfane
1202357-36-5

((4S,5R)-5-chlorooctan-4-yl)(phenyl)sulfane

Conditions
ConditionsYield
With N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.5h; Inert atmosphere; optical yield given as %ee;99%
thionyl chloride
7719-09-7

thionyl chloride

 1,7-dihydroxycarbonyl-1,7-dicarba-closo-dodecaborane
50571-15-8

1,7-dihydroxycarbonyl-1,7-dicarba-closo-dodecaborane

m-carborane-1,7-dicarboxylic acid dichloride
23810-52-8

m-carborane-1,7-dicarboxylic acid dichloride

Conditions
ConditionsYield
In thionyl chloride B compd. and SOCl2 placed into a flask under N2, refluxed for 24 h; evapd. (vac.); obtained as an oil;99%
thionyl chloride
7719-09-7

thionyl chloride

tris(8-carboxyl-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d′]bis[1,3]dithiol-4-yl)methyl radical sodium salt
372515-55-4

tris(8-carboxyl-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d′]bis[1,3]dithiol-4-yl)methyl radical sodium salt

C40H36Cl3O3S12
1079975-19-1

C40H36Cl3O3S12

Conditions
ConditionsYield
Stage #1: tris(8-carboxyl-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d′]bis[1,3]dithiol-4-yl)methyl radical sodium salt With triethylamine In chloroform at 20℃; for 0.5h;
Stage #2: thionyl chloride In chloroform at 20 - 50℃;
99%
thionyl chloride
7719-09-7

thionyl chloride

thallium chloride

thallium chloride

chlorine
7782-50-5

chlorine

thallium (III) chloride
13453-32-2

thallium (III) chloride

Conditions
ConditionsYield
In acetonitrile TlCl suspd. in CH3CN; Cl2 added under vigorous stirring; stirred for 30 min; soln. filtered; solvent evapd. in vacuum; SOCl2 added; evapd. after 10 min;98.5%
thionyl chloride
7719-09-7

thionyl chloride

tetrabenzyltin
10113-29-8

tetrabenzyltin

A

phenylmethanesulfinyl chloride
41719-05-5

phenylmethanesulfinyl chloride

B

dibenzyltin(IV) dichloride
3002-01-5

dibenzyltin(IV) dichloride

Conditions
ConditionsYield
In not given dropwise addn. of thionyl chloride to tetraalkyltin(IV) compd. under dry N2 atmosphere under ice cooling, warming to room temp., refluxing for 30 min; distn. (removal of excess of SOCl2), cooling resulting liquids, sepn., elem. anal.;A n/a
B 98%
thionyl chloride
7719-09-7

thionyl chloride

(29H,31H-2,9,16,23-tetracarboxyphthalocyaninato-N(29),N(30),N(31),N(32))cobalt(II)
69934-86-7

(29H,31H-2,9,16,23-tetracarboxyphthalocyaninato-N(29),N(30),N(31),N(32))cobalt(II)

cobalt tetra-4-(chlorocarbonyl)phthalocyanine
73533-44-5

cobalt tetra-4-(chlorocarbonyl)phthalocyanine

Conditions
ConditionsYield
In benzene a mixt. in dry benzene was refluxed for 7 h; filtered, washed with dry benzene, dried in a vac. at room temp.;98%
With pyridine In benzene at 80℃;96%
thionyl chloride
7719-09-7

thionyl chloride

2-chloro-4-(trifluoromethyl)-5-thiazolecarboxylic acid
72850-61-4

2-chloro-4-(trifluoromethyl)-5-thiazolecarboxylic acid

2-chloro-4-(trifluoromethyl)-5-thiazolecarbonyl chloride
72850-62-5

2-chloro-4-(trifluoromethyl)-5-thiazolecarbonyl chloride

Conditions
ConditionsYield
6 h refluxing with excess SOCl2;98%
thionyl chloride
7719-09-7

thionyl chloride

(m-carborane-9,10-diyl)diacetic acids
683816-30-0

(m-carborane-9,10-diyl)diacetic acids

(m-carboranyl-9,10-diyl)di(acetyl chlorides)
683816-32-2

(m-carboranyl-9,10-diyl)di(acetyl chlorides)

Conditions
ConditionsYield
In benzene byproducts: SO2, HCl; addn. of SOCl2 to soln. of (CH2COOH)2C2B10H10 in dry benzene at 20°C; heating for 2 h; cooling, removal of solvent and excess SOCl2 in vac.;98%
thionyl chloride
7719-09-7

thionyl chloride

C6H3F2N2(1+)*Cl(1-)
1489175-55-4

C6H3F2N2(1+)*Cl(1-)

2,3-difluorobenzenesulphonyl chloride
210532-24-4

2,3-difluorobenzenesulphonyl chloride

Conditions
ConditionsYield
Stage #1: thionyl chloride With copper(l) chloride In water at -5 - 20℃;
Stage #2: C6H3F2N2(1+)*Cl(1-) In water at -5℃; for 0.5h;
98%

7719-09-7Downstream Products

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